HCID 22872556, compound → HCID 53719778, compound
Reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([O:14][CH2:15][O:16][C@H:17]1[CH2:43][CH2:42][C@@:41]2([CH3:44])[C@@H:19]([C@@H:20]([OH:46])[CH2:21][C@@H:22]3[C@@H:40]2[CH2:39][CH2:38][C@@:37]2([CH3:45])[C@H:23]3[CH2:24][C@@H:25]3[O:30][C@@:29]4([O:36][CH2:35][C@H:33]([CH3:34])[CH2:32][CH2:31]4)[C@@H:27]([CH3:28])[C@@H:26]32)[CH2:18]1)[CH3:13]>ClCCl>[CH2:12]([O:14][CH2:15][O:16][C@H:17]1[CH2:43][CH2:42][C@@:41]2([CH3:44])[C@@H:19]([C:20](=[O:46])[CH2:21][C@@H:22]3[C@@H:40]2[CH2:39][CH2:38][C@@:37]2([CH3:45])[C@H:23]3[CH2:24][C@@H:25]3[O:30][C@@:29]4([O:36][CH2:35][C@H:33]([CH3:34])[CH2:32][CH2:31]4)[C@@H:27]([CH3:28])[C@@H:26]32)[CH2:18]1)[CH3:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Pyridinium chlorochromate (1.98 g, 9.20 mmol) was added to a mixture of (3β,5α,6α,25R)-3-ethoxy methoxy-6-hydroxyspirostane (0.90 g, 1.8 mmol) and celite (8.0 g) in anhydrous dichloromethane at 0° C. The reaction mixture was gradually warmed to ambient temperature over 1 hour and allowed to stir for an additional 5 hours. The reaction mixture was then filtered through a plug of silica gel using ether as the eluent. The combined ether fractions were concentrated in vacuo to afford 0.80 g (91%) of the title compound as a colorless solid. 1H NMR (250 MHz; CDCl3) d 4.75 (m, 2H); 4.4 (m, 1H); 3.6 (q, 2H, J=7.0 Hz); 3.45 (m, 2H); 3.35 (t, 1H, J=11.0 Hz); 2.4-0.6 (m, 40H); 0.9 (d, 3H, J=7.0 Hz); 0.8 (d, 3H, J=7.0 Hz); 0.78 (s, 6H). MS: 489.0 (M+H)+ ; mp 191-1930C.
Workup
- filtrationThe reaction mixture was then filtered through a plug of silica gel
- concentrationThe combined ether fractions were concentrated in vacuo
Sources & evidence
- ORD record
- ord-136977738e854bc8abcab7f1788a61d7
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05629295
Reaction notes
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